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1 Supporting Information Jamaicensamide A, a Peptide Containing β-amino-α-keto and η-amino-thiazole-omologated Amino Acid Residues from the Sponge Plakina jamaicensis Matthew T. Jamison and Tadeusz F. Molinski*,, Department of Chemistry and Biochemistry, and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, 9500 Gilman Dr. MC-0358, La Jolla, California Page Title Content S1 Figure S1 Structures of azole-homologated cyclic peptides from Theonella, Discodermia and Plakina jamaicensis. S2 S3 Preparation of Isoleucic Acid Standards and LC Analysis of their 2-aphthacyl Esters (S1 S4) S3 Antifungal Microbroth Dilution Assay S4 Figure S2 PLC Chromatograms of 2 -aphthacyl esters S1 S4 S5 Figure S3 FTIR (ZnSe) spectrum of jamaicensamide A (3). S5 Figure S4 ECD spectrum of jamaicensamide A (3). [C 3 C, 23 C, c = 1.44 x 10 4 M]. S6 Figure S5 LCMS of Marfey s analysis of 3 ozonolysis hydrolysate (SIM) S7 Figure S6 LCMS of Marfey s analysis of 3 a- 2 2 hydrolysate (SIM) S8 Figure S7 LCMS of L- and D-FDAA-amino acid standards (SIM) S9 Figure S8 1 MR spectrum of 3 (600 Mz, DMS-d 6 ) S10 Figure S9 DQF-CSY spectrum of 3 (600 Mz, DMS-d 6 ) S11 Figure S10 gsqc (multiplicity edited) spectrum of 3 (600 Mz, DMS-d 6 ) S12 Figure S11 gmbc spectrum of 3 (600 Mz, DMS-d 6 ) S13 Figure S12 gresy spectrum of 3 (600 Mz, t m = 300 ms, DMS-d 6 ) S14 Figure S13 gtcsy spectrum of 3 (600 Mz, t m = 75 ms, DMS-d 6 ) S15 Figure S14 1 MR spectrum of L-Isoleucic acid 2-aphthacyl Ester (S1, 500 Mz, CDCl 3 ) S16 Figure S15 13 C MR spectrum of L-Isoleucic acid 2-aphthacyl Ester (S1, 125 Mz, CDCl 3 ) S17 Figure S16 1 MR spectrum of D-Isoleucic acid 2-aphthacyl Ester (S2, 500 Mz, CDCl 3 ) S18 Figure S17 13 C MR spectrum of D-Isoleucic acid 2-aphthacyl Ester (S2, 125 Mz, CDCl 3 ) S19 Figure S18 1 MR spectrum of L-allo-Isoleucic acid 2-aphthacyl Ester (S3, 500 Mz, CDCl 3 ) S20 Figure S19 13 C MR spectrum of L-allo-Isoleucic acid 2-aphthacyl Ester (S3, 125 Mz, CDCl 3 ) S21 Figure S20 1 MR spectrum of D-allo-Isoleucic acid 2-aphthacyl Ester (S4, 500 Mz, CDCl 3 ) S22 Figure S21 13 C MR spectrum of D-allo-Isoleucic acid 2-aphthacyl Ester (S4, 125 Mz, CDCl 3 )
2 Figure S1. Structures of azole-homologated cyclic peptides from Theonella, Discodermia and Plakina jamaicensis. Type 1 Keramamide B 4 C 4 D 4 E 1 M R 3 Pro Tle* R 3 R R 1 2 R 2 13 R 4 Ile Thl R 1 = R 2 = Et, R 3 = R 1 = Et, R 2 = Me, R 3 = R 1 = Me, R 2 = Me, R 3 = R 1 = Me, R 2 = Et, R 3 = R 1 = Me, R 2 = Me, R 3 = S 3 R 1 = Me, R 2 = Et, R 3 = S 3 Br Br--Trp # " B $! % 1 A 9 rbiculamide A 9 Discobahamin A 7 10 Me S 5 1 7a B 7 7b 13 R 1 Tle* Thl R 1 = Br, R 2 =R 3 =R 4 = R 1 =R 2 =, R 3 = Me, R 4 = R 1 =, R 2 =R 3 = Me, R 4 = 9 Jamaicensamide A 3 11 Type 2 Ise Keramamide F 5 2a 13S, 1' G 1 2b 13R, 1' J S Gln 2 Ile Ala Thi 13 9 Dpr S 1' Ile Dpr Ala --Trp L-Thi 15 S Me Me Ise * Tle = theoleucine 9 Ise = isoserine Thi = theoisoleucine Thl = theonalanine 9 2 Ile Ala Thi 13 Dpr S R 3 R 1 R 2 Keramamide 1 K 2 Ile Ala D-Thi 15 Gln Dpr S Me R 1 =, R 2 = Br, R 3 = R 1 = Me, R 2 =, R 3 = Me Trp Calyxamide A 10a (15S) Trp Calyxamide B 10b (15R) 1. Kobayashi, Tetrahedron 1995, 51, Kobayashi, Tetrahedron 1998, 54, Kobayashi, JCS Perkin Trans. I 1991, Kobayashi, J. Am. Chem. Soc. 1991, 113, Kobayashi, J. rg. Chem. 1992, 57, Wakimoto, J. at. Prod. 2012, 75, Pomponi, J. at. Prod. 1994, 57, Kobayashi, Tetrahedron 1999, 55, Fusetani, J. Am. Chem. Soc. 1991, 113, Faulkner, J. at. Prod. 1997, 60, Jamison and Molinski, this work tp Me L-Phe L-Lys L-Leu R Mozamide A 10 B 10 Me MeCht L-Leu Cl Me L-Leu L-Phe L-allo-Ile R = Me R = Et L-Lys Keramamide L 2 Type 3 A 3 L-Phe R = R = R = S1
3 Preparation of L-, D-, L-allo, and D-allo-Isoleucic Acid Standards and Analysis of their aphthacyl Esters (S1-S4) D-allo-isoleucic acid was prepared from L-Ile following the procedure by Yajima and coworkers. 1 Acetylation (Ac 2, Ac) with concomitant racemization was carried out on L- or D-Ile, followed by fractional crystallization, of the corresponding + 4 salts, giving the less soluble D- and L-allo-Ile ammonium salts, which were converted to neutral -Ac amino acids with precipitation (1 M Cl to p 1). The acetamides were subjected to hydrolysis (2 M Cl, 80 C), then neutralization (Et 3, precipitation, recrystallization) to yield pure amino acids. Diazotization-hydrolysis of L-Ile, D-Ile, L-allo-Ile or D-allo-Ile (a 2, 2 M 2 S 4 5 C) 2 gave pure samples of L-, D-, L-allo-Ile and D-alloisoleucic acids (Ilea), respectively. The Ilea stereoisomers were converted to their corresponding 2-naphthacyl esters according to our published procedure 3 (Et 3, EtAc, α-bromo-2-acetylnaphthalene) and resolved by PLC under optimized conditions (Phenomenex Lux Cellulose-1, 5µ, mm, 75:25 n-hexane:i-pr, isocratic 30 min, 0.7 ml/min). The configuration and retention times (t R ) of the 2-naphthacyl esters of isoleucic acids were as follows: L- S1 (24.3 min), D-S2 (14.9 min), L-allo-S3 (20.5 min), and D-allo-S4 (15.5 min). L-S1 D-S2 L-allo-S3 D-allo-S4 L-Ilea-2-aphthacyl Ester (S1): Colorless glass; [α] D (c 1, CCl 3 ); UV-vis (CCl 3 ) λ max 245 nm (ε, log ), 251 nm (ε, log ), 286 nm (ε, log ), 295 nm (ε, log ), 336 nm (ε, log ); FTIR (ATR, ZnSe plate) ν 3480 (broad), 2970, 2938, 2874, 1743, 1698, 1469, 1377, 1180, 1125, 940, 822 cm 1 ; 1 MR (CDCl 3 ) δ 8.43 (s, 1) (m, 4), 7.64 (ddd, 1, J = 0.9, 7.3, 7.3 z), 7.59 (ddd, 1, J = 0.9, 7.3, 7.3 z), 5.63 (d, 1, J = 16.2 z), 5.54 (d, 1, J = 16.2), 4.32 (d, 1, J = 3.8 z), 1.99 (m, 1), 1.57 (m, 1), 1.34 (m, 1) 1.10 (d, 3, J = 6.9 z), 0.97 (t, 3, J = 7.4 z); 13 C MR (CDCl 3 ) δ 191.2, 174.5, 136.0, 132.4, 131.3, 129.6, 129.5, (2C), 127.9, 127.1, 123.2, 75.0, 66.6, 39.1, 23.6, 15.3, 11.8; RESITFMS m/z [M+a] + (calcd for C a +, ). D-Ilea-2-aphthacyl Ester (S2): Colorless glass; [α] D 22.3 (c 1, CCl 3 ); UV-vis (CCl 3 ) λ max 245 nm (ε, log ), 251 nm (ε, log ), 286 nm (ε, log ), 295 nm (ε, log ), 336 nm (ε, log ); FTIR (ATR, ZnSe plate) ν 3487 (broad), 2966, 2935, 2874, , 1470, 1377, 1182, 1125, 822 cm 1 ; 1 MR (CDCl 3 ) δ 8.43 (s, 1), (m, 4), 7.64 (ddd, 1, J = 0.9, 7.3, 7.3 z), 7.59 (ddd, 1, J = 0.9, 7.3, 7.3 z), 5.63 (d, 1, (1) Yajima, T.; orikawa, T.; Takeda,.; Takemura, E.; attori,.; Shimazaki, Y.; Shiraiwa, T. Tetrahedron: Asymmetry 2008, 19, (2) Müller, J.; Feifel, S. C.; Schmiederer, T.; Zocher, R.; Süssmuth, R. ChemBioChem 2009, 10, (3) Molinski, T. F.; Reynolds, K. A.; Morinaka, B. I. J. at. Prod. 2012, 75, S2
4 J = 16.2 z), 5.54 (d, 1, J = 16.2), 4.32 (d, 1, J = 3.8 z), 1.99 (m, 1), 1.57 (m, 1), 1.34 (m, 1) 1.10 (d, 3, J = 6.9 z), 0.97 (t, 3, J = 7.4 z); 13 C MR (CDCl 3 ) δ 191.2, 174.5, 136.0, 132.4, 131.3, (2C), (2C), 127.9, 127.1, 123.2, 75.0, 66.6, 39.1, 23.6, 15.3, 11.8; RESITFMS m/z [M+a] + (calcd for C a +, ). L-allo-Ilea-2-aphthacyl Ester (S3): Colorless glass; [α] D 21.3 (c 1.1, CCl 3 ); UV-vis (C 3 C) λ max 241 nm (ε, log ), 241 nm (ε, log ), 248 nm (ε, log ), 273 nm (ε, log ), 283 nm (ε, log ), 293 nm (ε, log ), 332 nm (ε, log ), 342 nm (ε, log ); FTIR (ATR, ZnSe plate) ν 3504, 2969, 2938, 2877, 1746, 1699, 1468, 1374, 1181, 1142, 824, 747 cm 1 ; 1 MR (CDCl 3 ) δ 8.43 (s, 1), (m, 4), 7.64 (ddd, 1, J = 0.9, 7.3, 7.3), 7.59 (ddd, 1, J = 0.9, 7.3, 7.3), 5.65 (d, 1, J = 16.2 z), 5.53 (d, 1, J = 16.2), 4.43 (d, 1, J = 2.8 z), 2.02 (m, 1), 1.62 (m, 1), 1.42 (m, 1), 1.00 (t, 3, J = 7.4 z), 0.98 (d, 3, J = 6.8 z); 13 C MR (CDCl 3 ) δ 191.3, 175.0, 135.9, 132.3, 131.2, (2C), (2C), 127.9, 127.2, 123.1, 73.1, 66.6, 38.6, 26.1, 13.1, 11.9; RESITFMS m/z [M+a] + (calcd for C a +, ). D-allo-Ilea-2-aphthacyl Ester (S4): Colorless glass; [α] D 22.0 (c 1.0, CCl 3 ); UV-vis (CCl 3 ) λ max 245 nm (ε, log ), 251 nm (ε, log ), 286 nm (ε, log ), 295 nm (ε, log ), 336 nm (ε, log ); FTIR (ATR, ZnSe plate) ν 3487 (broad), 2966, , 1743, 1698, 1470, 1377, 1189, 1126, 821 cm 1 ; 1 MR (CDCl 3 ) δ 8.42 (s, 1) (m, 4), 7.64 (ddd, 1, J = 0.9, 7.3, 7.3 z), 7.59 (ddd, 1, J = 0.9, 7.3, 7.3 z), 5.63 (d, 1, J = 16.2 z), 5.53 (d, 1, J = 16.2), 4.43 (d, 1, J = 2.7 z), 2.02 (m, 1), 1.61 (m, 1), 1.42 (m, 1) 1.01 (t, 3, J = 7.4 z), 0.99 (d, 3, J = 6.3 z); 13 C MR (CDCl 3 ) δ 191.3, 175.0, 136.0, 132.4, 131.3, (2C), (2C), 127.9, 127.2, 123.2, 73.1, 66.6, 38.6, 26.1, 13.1, 11.9; RESITFMS m/z [M+a] + (calcd for C a +, ). Antifungal Microbroth Dilution Assay. Serial dilutions were prepared with a solution of drug in DMS (10 µl) and Difco Antibiotic Medium #3 (BD) (240 µl) and dispensed into the wells of clear polystyrene 96-well plates. 4 A two-fold dilution series was prepared from the stock solution (125 µl) across 12 wells for each compound tested. vernight liquid cultures of Candida albicans ATCC and Cryptococcus gattii were diluted to an D of (λ = 590 nm). Aliquots (125 µl) of each diluted culture added to each well in separate plates and the final volume (250 µl) made up with medium. The D of each well was measured after further incubation (35 C, 48 h). on-linear regression was applied to fit the D data to a sigmoidal curve and extract MIC 50 and the MIC 90 values were calculated using a ill slope of 4. 5 (4) CLSI. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts. Approved Standard 3rd Edition; CLSI document M27-A3; Clinical and Laboratory Standards Institute, Wayne, PA, (5) Brown, A. M. Comp. Meth. Prog. Bio. 2000, 65, S3
5 Figure S2. PLC Chromatograms of 2 -aphthacyl esters S1-S4 (a)-(d). Phenomenex Lux Cellulose-1, 5µ, mm, 75:25 hexane: i-pr, isocratic 30 min, 0.7 ml/min, UV 254 nm. (a) (b) Co-injection of L-Isoleucic acid 2-aphthacyl Ester (S1) and D-Isoleucic acid 2-aphthacyl Ester (S2) D-Isoleucic acid 2-aphthacyl Ester (S2) (c ) (d) L-allo-Isoleucic acid 2-aphthacyl Ester (S3) D-allo-Isoleucic acid 2-aphthacyl Ester (S4) S4
6 Figure S3. FTIR (ZnSe) spectrum of jamaicensamide A (3). Figure S4. ECD spectrum of jamaicensamide A (3). [C 3 C, 23 C, c = 1.44 x 10 4 M] !" " !" / mol -1 dm -3 cm " # /nm S5
7 Figure S5. LCMS Marfey s analysis of 3 ozonolysis hydrolysate (SIM) (a) (a) L-FDAA-L-alanine SIM m/z = 342 (b) (b) L-FDAA-L-2- aminobutyric acid SIM m/z = 356 (c) (c) L-FDAA-L-proline SIM m/z = 368 (d) (d) L-FDAA-L-aspartic acid SIM m/z = 386 (e) (e) α - δ -L-FDAA-Lornithine SIM m/z = 637 S6
8 Figure S6. LCMS Marfey s analysis of 3 a- 2 2 hydrolysate (SIM) (a) (a) L-FDAA-L-alanine SIM m/z = 342 (b) (b) L-FDAA-L-2- aminobutyric acid SIM m/z = 356 (c) (c) L-FDAA-L-proline SIM m/z = 368 (d) (d) L-FDAA-L-2- aminopentanoic acid SIM m/z = 370 (e) (e) α - δ -L-FDAA-Lornithine SIM m/z = 637 S7
9 Figure S7. LCMS of L-FDAA-amino acid standards (SIM) L- FDAA- (L- and D-)- aspartic acid SIM m/z = 386 (a) L- FDAA- (L- and D-)- alanine SIM m/z = 342 (b) L- FDAA- (L- and D-)- proline SIM m/z = 368 (c) L- FDAA- (L- and D-)- 2- aminopentanoic acid SIM m/z = 370 (d) L- FDAA- (L- and D-)- ornithine SIM m/z = 637 (e) L- FDAA-L- 2- aminobutyric acid SIM m/z = 356 (f) L- FDAA- D- 2- aminobutyric acid SIM m/z = 356 (g) S8
10 Figure S8. 1 MR spectrum of 3 (600 Mz, DMS-d 6 ) ppm S9
11 Figure S9. DQF-CSY spectrum of 3 (600 Mz, DMS-d 6 ) S10
12 Figure S10. gsqc (multiplicity edited) spectrum of 3 (600 Mz, DMS-d 6 ) S11
13 Figure S11. gmbc spectrum of 3 (600 Mz, DMS-d 6 ) (600 S12
14 Figure S12. gresy spectrum of 3 (600 Mz, t m = 300 ms, DMS-d 6 ) S13
15 Figure S13. gtcsy spectrum of 3 (600 Mz, t m = 75 ms, DMS-d 6 ) S14
16 Figure S14. 1 MR spectrum of L-Isoleucic acid 2-aphthacyl Ester (S1, 500 Mz, CDCl 3 ) ppm S15
17 Figure S C MR spectrum of L-Isoleucic acid 2-aphthacyl Ester (S1, 125 Mz, CDCl 3 ) ppm S16
18 Figure S16. 1 MR spectrum of D-Isoleucic acid 2-aphthacyl Ester (S2, 500 Mz, CDCl 3 ) ppm S17
19 Figure S C MR spectrum of D-Isoleucic acid 2-aphthacyl Ester (S2, 125 Mz, CDCl 3 ) ppm S18
20 Figure S18. 1 MR spectrum of L-allo-Isoleucic acid 2-aphthacyl Ester (S3, 500 Mz, CDCl 3 ) ppm S19
21 Figure S C MR spectrum of L-allo-Isoleucic acid 2-aphthacyl Ester (S3, 125 Mz, CDCl 3 ) ppm S20
22 Figure S20. 1 MR spectrum of D-allo-Isoleucic acid 2-aphthacyl Ester (S4, 500 Mz, CDCl 3 ) ppm S21
23 Figure S C MR spectrum of D-allo-Isoleucic acid 2-aphthacyl Ester (S4, 125 Mz, CDCl 3 ) ppm S22
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